Top Definition
A quite pleasurable sex act involving a "crew" of three consenting adults of legal age. In order to perform the Sneaky Sailboat, you need a Captain, a Wench, and a First Mate. The captain and the wench begin intercourse in the captain's quarters while wearing sailor hats. NOTE: it is imperative that the partners do the nasty while standing in order to create the "mast" for the actual sailboat. When the seaman is halfway to Port Jizztown, he lets out a hearty yell of "hoist the sails" at which point he throws a bed sheet over the wench's head, thus blinding and disorienting her. At this point the First Mate relieves the captain of his duties and brings with him the "sneaky" aspect of the event. In a manner similar to a Houdini or a Prestige, the Captain pulls out and leaves the room. The First Mate, who until this point has remained hidden, reveals himself, yells "Avast ye scurvy dogs!" and proceeds to steal the booty and dock his member in the wench's rear port. When properly executed, a Sneaky Sailboat can be great fun at parties, family gatherings and childrens' birthdays.
Captain: Dude, there's nothing on tv tonight, what should we do?
First Mate: I don't know we could always call that girl from the party last weekend and try and pull off the Sneaky Sailboat.
Captain: Yeah that's a great idea, and so wholesome too.
by captainjackoff October 16, 2011

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